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8.52185

Fmoc-Asn(Trt)-Ser(psiMe,Mepro)-OH

Novabiochem®

Synonym(s):

Fmoc-Asn(Trt)-Ser(psiMe,Mepro)-OH

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About This Item

Empirical Formula (Hill Notation):
C44H41N3O7
CAS Number:
920519-33-1
Molecular Weight:
723.81
MDL number:
MFCD10001368
UNSPSC Code:
12352209
NACRES:
NA.22
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Quality Level

200

product line

Novabiochem®

assay

≥95% (TLC), ≥97.0% (HPLC)

form

powder

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

manufacturer/tradename

Novabiochem®

application(s)

peptide synthesis

functional group

hydroxyl

storage temp.

2-8°C

SMILES string

N7(C(OCC7C(=O)O)(C)C)C(=O)C(NC(=O)OCC4c5c(cccc5)c6c4cccc6)CC(=O)NC(c3ccccc3)(c2ccccc2)c1ccccc1

InChI

1S/C44H41N3O7/c1-43(2)47(38(28-54-43)41(50)51)40(49)37(45-42(52)53-27-36-34-24-14-12-22-32(34)33-23-13-15-25-35(33)36)26-39(48)46-44(29-16-6-3-7-17-29,30-18-8-4-9-19-30)31-20-10-5-11-21-31/h3-25,36-38H,26-28H2,1-2H3,(H,45,52)(H,46,48)(H,50,51)

InChI key

CURRWEJPHUVJFC-UHFFFAOYSA-N

General description

This pseudoproline dipeptide is undoubtedly the most effective and simplest to use tool for overcoming aggregation and enhancing peptide quality in Fmoc SPPS for peptide containing the Asn-Ser dipeptide motif. It consists of a dipeptide in which the serine residue has been reversibly protected as a structure-breaking proline-like TFA-labile oxazolidine. The reason pseudoproline residue is introduced as a dipeptide is because it avoids the need to acylate the hindered oxazolidine nitrogen. This has the added advantage of extending the peptide chain by two residues in one step. The serine residue is regenerated during the normal TFA-mediated cleavage reaction.

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS
Overcoming Aggregation in Fmoc SPPS

Analysis Note

Color (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Optical rotation α 25/D (c=1 in methanol): -31.0 - -26.0 °
Purity (TLC(157A)): ≥ 95 %
Purity (TLC(CMA2)): ≥ 95 %
Assay (HPLC, area%): ≥ 97.0 % (a/a)
Acetate (IC): ≤ 0.1 %
Ethyl acetate (HS-GC): ≤ 2.0 %

To see the solvent systems used for TLC of Novabiochem® products please click here.

Other Notes

Replaces: 05-20-1010

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Protocols

Overcoming Aggregation in Solid-phase Peptide Synthesis

The ease of assembly of a given peptide sequence is hard to predict, which makes peptide synthesis challenging. Review methods and reagents for avoiding aggregation in solid-phase peptide synthesis.

Global Trade Item Number

SKUGTIN
852185000104027269092825
852185002504027269189990
852185000504027269092832